


Shall We?

by xenteaa



Category: The Umbrella Academy (Comics), The Umbrella Academy (TV)
Genre: F/M, Reader Insert, imagine
Language: English
Status: Completed
Published: 2020-10-09
Updated: 2020-10-09
Packaged: 2021-03-07 17:00:24
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,388
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26911039
Author URL: https://archiveofourown.org/users/xenteaa/pseuds/xenteaa
Summary: i got a request on tumblr so i thought i might as well post it here!"Hi! If it’s not too much trouble, can I request a Five x fem! Reader? A angsty fic where Five rejects the reader because he wants protect her from all the problems him and his family are involved in? Giving The Handler and opportunity to hire the reader at The Commission and use her against Five? Thank you!"
Relationships: Five Hargreeves & Reader, Number Five | The Boy (Umbrella Academy) & Reader, Number Five | The Boy (Umbrella Academy)/Original Female Character(s), five hargreeves/reader
Comments: 3
Kudos: 58





	1. Chapter 1

**Author's Note:**

> For the sake of the story, Five disappeared when he was 18 (instead of 13) and got stuck in his 18 year-old-body after coming back accordingly. Also I’ve decided to give the reader and the Handler kind of a Lila x the Handler dynamic  
> The events are taking place in s1, some details of the canon are obvsly altered. Hope you enjoy!

The last couple of months have been difficult, to say the least. On top of losing yet another job alongside any hope of a bright and successful future, you also realized you hardly had any friends by your side anymore. As the mundane took over your days, you simply grew apart and you didn’t even notice it happen.

Adult life wasn’t nearly as exciting as you always imagined it to be as a child. In fact, ever since Five’s disappearance everything kind of went downhill.

_Five Hargreeves was your closest and dearest friend ever since you two randomly met at some cafe. He sneaked out of the Academy to have a few hours of peace to study and enjoy his coffee that day, and you were there merely observing._

_Just like there are people who call themselves bird-watchers, you believed human-watching was a thing too. Not in a creepy way, of course. You simply enjoyed being around people - you found them curious, something to observe and study. It was like there were multiple worlds, entire universes sitting behind each table, disguised and restricted by the limitations of a human body.  
Naturally, Five caught your eye. You weren’t brave enough to start a conversation at the time, not wanting to disturb him and distract him from his seemingly important business, but he couldn’t help but notice your borderline polite staring and spoke to you first._

_“Want an autograph or something?”_

_“Aren’t you modest. Sorry to disappoint but I have no idea who you are, pretty boy.”_

_He liked you right away._

Without Five life sort of… stopped being fun. There were things to do and explore, sure, and you’ve met many wonderful people over the years but nobody quite managed to make you feel like Five could. _At home._

You couldn’t help but notice you were experiencing life on autopilot, your mind somewhere else. It felt like some part of you had disappeared with Five and you weren’t able to find it or replace it ever since. 

Today was an exceptional day. You got your heart broken for the second time, funnily enough, by the very same person. As you were numbly walking down the street without much purpose, you got caught in the pouring rain. Cold heavy drops were dripping onto your scalp and driving you crazy with each passing second which mildly resembled Chinese water torture, and you chuckled at the thought. Seemed appropriate. 

_“Jesus Christ, Y/N, don’t you get it? You’re ordinary. You’re not special. You can’t help,” Five spat out, hectically moving around the kitchen mere minutes after your neither impressive nor moving reunion._

_“What, you just want me to walk away and do nothing, then?” you asked, absolutely baffled by how casually Five dismissed your existence as if you were total strangers and you just happened to come by._

_“Yes, that’s exactly what I want. I have enough on my plate already, I don’t need another inconvenience. There’s already five of them in the room,” he briefly pointed at his siblings and ignored their attempts to argue, “Go.”_

At this point, you could probably write a whole trilogy on how to get your heart smashed into a million pieces and still somehow remain a functioning social unit. Well, barely, if you were being honest. 

You couldn’t tell if you were sad or angry and you didn’t know what hurt you more - Five acting cold and pretending like you were absolutely no one to each other, Five neglecting you as a whole because, apparently, you were a little too useless to even be in the house you used to call your second home or the fact that all those years of wishing he’d come back, hug you tight and never leave your side again were nothing more than a naive stupid fantasy. Evidently, you weren’t as important to him as you thought you were, after all. 

Lost in your own thoughts, you weren't paying attention to your surroundings and ended up bumping into some very well-dressed lady, almost knocking her off her high heels.

“Oh, sorry,” you muttered, half annoyed, half apologetic.   
“Ah, look at you. You don’t seem very happy, dear,” she pointed out, the tone of her voice weirdly welcoming and almost mother-like. Caring? You finally looked up to face her. 

Her fashion sense seemed a bit out of touch with the current times but it looked stunning nonetheless, making her person a bit too eccentric to overlook. 

“Bad day. Happens to the best of us, huh?” you tried to politely brush it off and be on your merry way, the only thing on your mind now being a bottle of whiskey you had in your fridge. But your plans didn’t really correspond with hers, it seemed.

“Would you care to join me for dinner, sweetheart? I think you’re in need of some nice food and dry clothes,” she said as she wrapped her arm around your shoulder and squeezed it a little in a reassuring manner. 

Things like that didn’t happen every day. In fact, they barely happened at all, considering how indifferent people were to other people’s problems, hardly ever concerned about anything other than their own well-being. 

Something about the suggestion felt off but you were drowning in your pain a little too much to hear what your gut was trying to tell you. Usually, your instincts and intuition were more than reliable but you had a very unhealthy habit of ignoring them altogether. So you agreed, pushing aside the remnants of your dignity and desire to look like you weren’t completely desperate.

You spent the rest of your evening at a five star hotel where the lady was apparently staying. The suite was huge and the room service was _flawless_. She offered you some dry clothing and listened to your story. You weren’t the type to pour your heart out to strangers but tonight was probably your rock-bottom, so you couldn’t care less. At least one person in the world was showing you kindness and acknowledgement and you couldn’t resist giving into the much needed feeling of being heard. One thing was still nagging at you, though.

The woman had this strange, almost palpable aura around her - you couldn’t quite put your finger on it but it felt like she was and wasn’t trust-worthy all at once. Her caring eyes and engaged body language were telling you she was a good person and genuinely wanted to help but something about her was a titch too perfect. Too sweet to be true.

“Oh, God, it’s so late. I’m sorry, I didn’t realize,” you sighed as you looked at the clock on the wall. You didn’t want to come across as impolite or ungrateful, so you began to collect your things when the woman got up and approached you, gently placing her hand on your forearm. 

“Please, darling. It was my pleasure,” she said, giving you a warm smile, “Oh, how rude of me. All this time and I haven’t introduced myself! I’m the Handler.”

\---

It’s been about two years since you’ve been recruited at the Commission. 

The Handler was truly exceptional at manipulating, and it didn’t take her long to convince you to join. She had been watching your relationship with Five long before finally making her move and bumping into you at just the right time. Plus, it was fairly easy to take advantage of someone who had nowhere to go and was absolutely devastated by a gone-wrong friendship, the most brilliant thing of it all being the fact that to you - it all looked like a gift from fate itself.

Arriving at the Commission for the first time left you feeling like a 6-year-old kid at a chocolate factory, the entirety of space-time continuum at your service. Being part of it felt like a dream come true as you finally became part of something grand and significant, feeling noticed and appreciated, and the Handler’s ever so strategic sweetness and praise were only pushing you to fall deeper into her trap. It wasn’t all her doing, though. You were a rather short-tempered individual and your pain tended to convert into rage pretty quickly. Conveniently, working for the Commission was the _perfect_ place for you to set this overflowing anger loose under the excuse of a noble goal. You were protecting the timeline, after all, this sure should pardon your ways of doing so.

Needless to say, you were completely brainwashed - your emotional vulnerability and still unhealed wounds serving as perfect strings for the Handler to pull and play you like a puppet. 

It was a calm sunny day outside as you were having lunch in her office - a habit you’ve developed almost instantly and never quite got rid of it. Your heavy boots landed on the table as you were sitting comfortably in your chair, chewing on your takeaway and feeling weirdly peaceful for someone whose job was assassinating people.

“I have a new assignment for you, darling,” the Handler said matter-of-factly, handing over a folder full of files over the table. Your heart skipped a beat as you opened it and laid your eyes on the picture of your new victim.   
“You can’t be serious,” you almost choked on air, suddenly feeling too nauseous to finish your food.

“What? Why? Hazel and Cha-Cha are failing miserably, and you’re the next best we have! Help your collegues out,” she shrugged casually as if you weren’t talking about _Five fucking Hargreeves._

“Come on, wasn’t he the one breaking your heart in the first place, little one?” she added, a sly light twinkling in her eyes as her lips curved in a knowing smirk.

_“You’re not special.”_

_“You’re an inconvenience.”_

_“Jesus, just GO.”_

You would be lying if you said Five’s words weren’t playing in your head like a broken record every single goddamn day of your existence.   
You used to cherish your time with Five dearly, always giving it a very special place in your palace of memories yet now it was ruined and painted over with much darker colors, this area of your mind bleeding with hostility and regret, rage and bitterness, and more importantly - utter confusion as to _why_ you were rejected by him. Part of you wanted to prove to him you weren’t as useless as he thought you were. Maybe, that was the reason for your restless training sessions and consequently quick success at your job at the Commission. 

“Okay,” you said sternly and quickly got up from your chair, throwing your unfinished lunch in the trashcan and slamming the door behind yourself as you left the Handler’s office.

\---

The best thing about the Commission was the fact that they didn’t lie when they said “you have all the time in the world”. It was true - all it took was a simple briefcase and a push of a button. So, even though two years have passed for you, you could still pop in 2019, mere days after your reunion fiasko. 

The Handler was smart enough not to give you a briefcase of your own this time, travelling with you and then leaving you to do the job instead. She knew way too well that, If Five was to get his hands on the time-travelling device, her life would most definitely get a whole lot harder, so she took precautions.

Initially, you were sent to help Hazel and Cha-Cha since they were obviously failing, so you joined them the day they attacked the Academy. Unfortunately for all three of you, the entire Hargreeves family was in the house, and it made things way more complicated than you would prefer. 

As the Handler unfroze time and vanished, from an outsider’s perspective you basically appeared out of thin air with a blue flash of light, making everyone stop their fighting for a second and turn their heads to you, clearly surprised and confused. 

Agreeing to the job, you still weren’t sure if you could do what the Handler asked of you. Sure, you’ve been an assassin for a while now but your killing was never personal. It was merely a job and you always treated it like one. This time, however, it was very personal and to say you were feeling hesitant would be a huge understatement. Did you really want Five dead just because he didn’t need you? Were you really that petty after all, willing to kill someone you still loved out of childish resentment and bitterness? 

“Hi, Five,” you greeted him, making eye contact. He glanced at you and furrowed his eyebrows, evidently more puzzled than scared. Five figured something wasn’t right straight away, your sudden change of clothes from your usual baggy sweaters to a tight black turtleneck giving it away a tiny bit. 

You suddenly realized you haven’t seen him in so long you almost forgot the way he made you feel just by _looking_ at you. Jesus Christ, you needed to stop.

As the two of you were shamelessly staring at each other and approaching each other carefully, just like two animals circling each other, not knowing what to expect, everyone else sort of naturally returned to the fighting. Hazel against Diego, Cha-Cha against Allison, Luther still laying on the floor unconscious. 

“The hell are you doing here?” Five asked, his tone clearly accusatory and displeased.

“The Handler says hello,” you replied with a grin as you watched pure dread wash over his features. You could just see the cogs in his mind turning as he was putting two and two together, his eyes slowly getting filled with… regret? It’s always been quite a riddle to identify what emotion Five was having, and this exact moment was no exception.

It would have been a lot easier for you, of course, if only you knew how much it broke him to push you away in the first place. All those years in the apocalypse, and there wasn’t a single day when he didn’t miss you. Poor Delores was cursed to be hearing all about you almost every day. But you’d never know. 

Despite how naturally being mean came to Five, he was actually struggling to find the words to make you leave just a few days prior. So utterly afraid of losing you again he thought of nothing better than to simply push you away in order to protect you. In all fairness, it was a perfect plan - make you hate him for a week while he was running around saving the world, then come back, explain himself and apologize profusely. Apocalypse stopped, world saved, relationship restored, everything back to normal - nothing too difficult. 

However, Five didn’t factor the Handler into the picture, and now his good intentions were cruelly turned against him in a way that he could never even imagine was possible. The idea of you being sent to murder him didn’t scare him at all but the thought of you being turned into a killing machine was absolutely heartbreaking because Five knew all about it and wouldn’t wish this life upon anyone. Especially you.

He let you down. He properly messed up.

“You do know you can’t win. I really don’t wanna hurt you, Y/N,” he uttered, raising his hands a little as a way to warn you not to come any closer for your own good.   
Even though it was supposed to be a sweet gesture of concern, hearing him confirm that he still thought you were no match for him cut you to your very core.

“Oh, yeah? Well, I’m afraid you might have to. Shall we?” you sneered and threw your leg into the air, hitting Five right under his kneecap and making him collapse on the ground with a surprised gasp.


	2. Chapter 2

**Notes for the Chapter:**

> For the sake of the story, Five disappeared when he was 18 (instead of 13) and got stuck in his 18 year-old-body after coming back accordingly. Also I’ve decided to give the reader and the Handler kind of a Lila x the Handler dynamic  
> The events are taking place in s1, some details of the canon are obvsly altered. Hope you enjoy!

Five truly had zero intention of hurting you, but your determination to have a fight left him no choice, and even his clear advantage of having loads more experience and superpowers on top did not seem to make you hesitate.

“Come on, don’t be stupid, Y/N,” Five commented as he got back on his feet and took a few steps away from you, still giving you a chance to back off before he had to inflict any pain on your person, but all it achieved was winding you up even more.

The problem was - you two underwent identical training at the Commission as the Handler gave both of you her very best mentor, and right now you were basically mirroring each other’s moves, except Five was also using his spatial jumps to disorient you. He was still going easy on you, mostly just blocking your punches and jumping further away so you had to chase him all over the Academy while he was hoping you would simply exhaust yourself before any real damage would be done. Quite frankly, it was a smart decision on his part and a rather thoughtful one as well because, despite all appearances, he actually cared about you an awful lot.

As the both of you gracefully danced all the way to the second floor, you were already out of breath from the endless running around which meant Five’s plan was beginning to work. However, you realized what he was doing soon enough to indulge him into the feeling of being right and played his little game for a while, waiting for the perfect moment when he’d get distracted, and as the moment came you had to act fast.

You threw yourself forwards and promptly wrapped your arms around Five’s waist, knocking him off his feet and pressing your body against his as you pinned him to the floor. He groaned with annoyance and winced at the pain as his back hit the hard wooden surface. The next few seconds sort of happened in slow-mo for both of you as he roughly pushed you off himself and somehow managed to switch places with you, now looming over your body and warningly putting his knee on your solar plexus, threatening to crush your ribcage if you moved.

A mutual silence fell between you as you were processing the last 30 minutes of your lives, both visibly struggling to believe that each of you somehow ended up fighting the person they would never wish to hurt in their entire life. The sounds of your heavy breathing were filling the room as you were merely staring at each other in utter confusion. The weight of Five’s knee on your diaphragm was beginning to give you trouble breathing, and your breaths became shallow and hoarse which finally snapped him out of his trance.

“Gonna tell me what the hell is up now, Y/N?” he asked in his teacher-y manner that you used to absolutely hate and adore all at once, especially when he used to give you lectures on your occasional fuck-ups - whether it was failing a class because you were too lazy to turn in your assigments in time or something a little more serious, like getting into an argument with the Monocle and consequently making life harder for both of you.

You would always roll your eyes and smirk when he would get into his i-am-disappointed-in-you-but-i-still-love-you character and cross his arms on his chest for dramatic effect.

“You were the one telling me to piss off in the first place, remember,” you narrowed your eyes as you were subtly gasping for air underneath Five’s weight. He pursed his lips and looked away, contemplating whether or not to be completely honest. Evidently, his lack of sincerity got him nowhere the last time around, so he sighed loudly; his shoulders dropping and his expression finally revealing all of the exhaustion and regret that he was concealing quite successfully up until now.

“I only pushed you away to protect you.”

“Sounds like bullshit to me,” you replied, clearly unimpressed and palpably suspicious; two years of being brainwashed by the Handler now taking their toll on your perspective.

“God, don’t be so slow,” Five uttered clearly irritated but then quickly realized his offensive implication and added, “Said with respect.”

You stayed silent, raising your brow as a way of telling him to continue.

“I couldn’t risk you becoming a casualty because being involved in my family’s mess as a non-super _is dangerous_. As in, you’re going to be a target _all the time_ , and I couldn’t and still can’t afford to waste my time worrying about your safety. As much as I’d love to - it’s simply not the luxury I have. I’ve got to stop the end of the world, otherwise _everyone_ is going to be dead in four days, don’t you get it?” Five asked, a waterfall of emotions pushing at the inner sides of his chest, waiting to be set loose and consume everything on its way.

You were quietly listening to his explanation and taking it all in whilst still trying to fight off the suspicion and disbelief that were nagging at your every cell.  
“I wanted to keep you safe because I couldn’t bear to lose you again,” his voice trembled a little as the memories of his post-apocalypse life washed over his mind, “The last 45 years have been a _fucking_ nightmare.”

“I’d find it way more believable if you stopped crushing my ribs for starters,” you muttered through clenched teeth and immediately felt the pressure taken off your chest, precious and very much needed oxygen starting to flow through your system the way it should again.

Five got up and offered his hand to help you on your feet as a gesture to show you that he didn’t see you as an enemy and placed trust in you. You took his hand and steadied yourself awkwardly, still slightly disoriented and light-headed.

“I don’t know what the Handler told you but I do know she’s exceptional at manipulating,” Five added as he looked you right in the eye, “Christ, and you’re so naive, always have been. Most days it’s truly adorable but sometimes, Y/N, it really doesn’t work in your favor,” as the words escaped his lips, his gaze became noticeably softer; his expression blossoming with tenderness towards you.

“Prove it. Prove that you care.”

Five chuckled and shook his head, simultaneously annoyed and amused at your stubbornness. The atmosphere between you was shifting and you couldn’t help but notice the familiar overwhelming feeling of comfort and peace enveloping your person from head to toe. You’ve forgotten what it felt like being around Five, and now you were finally getting to remember. _At home._

He slipped his hand into the pocket of his uniform shorts and pulled out a grape-sized plastic figure of a golden retriever.

“You gave me this a few days before I jumped and got stuck in the future. I carried it with me all the way. This silly trinket was the only thing I had left of you, the only thing that reminded me you were still out there waiting for me. Kept me going,” he shrugged casually as if it wasn’t important at all which it _absolutely_ was.

_“Five, c’mere! Look what I found!” you called for him as you were sitting on the floor surrounded by all sorts of useless crap. You were in the middle of decluttering your bedroom when a little figure of a dog caught your eye, it was the breed that Five was especially fond of and you knew he secretly dreamed of getting a puppy of his own as soon as he was out of the house._

_“What’s that?” he asked, unimpressed._

_“It’s a doggie! He wants to be your friend,” you replied, playing with your accent a little, rolling you “r”s and shifting the flow of your words to sound more Scottish or ... Russian. God knows where you were going with it but you tended to butcher your accent for fun quite a lot._

_“Y/N, are you twelve?”_

_“His name is Mr.Pennycrumb and he’s gonna look after you whenever I’m not around,” you said with utmost confidence and gave him a wide smile, putting the trinket into Five’s pocket, clearly very proud of yourself and still committed to your silly accent performance, “Treat him well.”_

_Five scoffed and shrugged._

_“Whatever.”_

“So did he?” you asked, staring at the goddamn toy as tears were slowly welling up in your eyes.

“What?”

“Did he do a good job looking after you while I wasn’t around?” your gaze finally met Five’s as the realization in his own eyes was starting to sink in. A pained smile touched the corners of his mouth, and you could see Five genuinely struggle to maintain his tough facade.

“Yeah. He did.”

Without saying a word, you stepped closer and rested your cheek on his shoulder, wrapping your arms around him, this time with no hostility or murderous intention. If you had to be perfectly honest with yourself, you’d admit you could never find it in you to actually hurt Five, let alone killing him. Both of you knew that way too well.

He returned the hug and pulled you closer, burying his nose in your hair and then planting a quick innocent kiss on the top of your head. Feeling the warmth radiating from you was enough to make him relax further into your embrace, his eyes now closed shut and his breathing steady and deep.

It didn’t last for as long as you’d like, though, a big loud bang from downstairs making you both flinch and pull away from each other, breaking your fragile bubble of comfort and calm in an instant.

“Shit, Hazel and Cha-Cha,” Five whispered, concern and worry crawling back onto his features. He briefly looked at you, and you simply nodded, non-verbally confirming that you were willing to help and were no longer part of the Handler’s plan.

The two of you were going to talk all about that later. His years alone, his and your own involvement with the Commission, the end of the world and loads more.

Of course, right in this moment neither of you could possibly know that your friendship was, in fact, a gateway into a lifelong partnership but you were bound to find out eventually. And the journey you two were about to begin as soon as the apocalypse was dealt with and gone was going to be _magnificent._


End file.
